2-Bromo-6-phenylcyclohexanone → [3-Methoxy-4-(2-methyl-thiazol-5-yl)-phenyl]-(4-phenyl-4,5,6,7-tetrahydro-benzothiazol-2-yl)-amine

HRID 2076129Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2076129
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:15][C:16]([NH2:18])=[S:17])[CH:6]=[CH:7][C:8]=1[C:9]1[S:13][C:12]([CH3:14])=[N:11][CH:10]=1.Br[CH:20]1[CH2:25][CH2:24][CH2:23][CH:22]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:21]1=O>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:15][C:16]2[S:17][C:28]3[CH2:29][CH2:30][CH2:31][CH:26]([C:22]4[CH:23]=[CH:24][CH:25]=[CH:20][CH:21]=4)[C:27]=3[N:18]=2)[CH:6]=[CH:7][C:8]=1[C:9]1[S:13][C:12]([CH3:14])=[N:11][CH:10]=1

Komponenten

4

Edukt 2

HCID 127791292-Bromo-6-phenylcyclohexanoneHCID 86632612[3-Methoxy-4-(2-methyl-thiazol-5-yl)-phenyl]-thiourea

Produkt 1

HCID 44193860[3-Methoxy-4-(2-methyl-thiazol-5-yl)-phenyl]-(4-phenyl-4,5,6,7-tetrahydro-benzothiazol-2-yl)-amineAusbeute 94,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of [3-methoxy-4-(2-methyl-thiazol-5-yl)-phenyl]-thiourea (110 mg, 0.39 mmol) and 2-bromo-6-phenyl-cyclohexanone (105 mg, 0.41 mmol) in ethanol (4 ml) was heated to reflux over night. The precipitated solid was filtered off after cooling to room temperature and dried to yield the title compound (160 mg, 94%) as a yellow solid. MS ISP (m/e): 434.3 (100) [(M+H)+]. 1H NMR (DMSO-D6, 300 MHz): δ (ppm)=10.32 (br s, 1H, NH), 8.10 (s, 1H), 7.61 (s, 1H), 7.56 (d, 1H), 7.29 (t, 2H), 7.15-7.21 (m, 3H), 6.85 (d, 1H), 4.00 (m, 1H), 3.48 (s, 3H), 2.75 (m, 2H), 2.68 (s, 3H), 2.14 (m, 1H), 1.70-1.94 (m, 3H).

Aufarbeitung

  1. temperatureto reflux over night
  2. filtrationThe precipitated solid was filtered off
  3. customdried

Quellen und Nachweise

ORD-Eintrag
ord-7033ec88da9844b78e86bbcc5424bc2e
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07923450B2

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